Browse
Submit Data
Databases
API
Help

Dataset Information

20 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

The synthesis of ?-aryl-?-aminophosphonates and ?-aryl-?-aminophosphine oxides by the microwave-assisted Pudovik reaction.

ABSTRACT: A family of ?-aryl-?-aminophosphonates and ?-aryl-?-aminophosphine oxides was synthesized by the microwave-assisted solvent-free addition of dialkyl phosphites and diphenylphosphine oxide, respectively, to imines formed from benzaldehyde derivatives and primary amines. After optimization, the reactivity was mapped, and the fine mechanism was evaluated by DFT calculations. Two ?-aminophosphonates were subjected to an X-ray study revealing a racemic dimer formation made through a N-H···O=P intermolecular hydrogen bridges pair.

SUBMITTER: Balint E

PROVIDER: S-EPMC5238548 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction.

Bálint Erika E Tajti Ádám Á Ádám Anna A Csontos István I Karaghiosoff Konstantin K Czugler Mátyás M Ábrányi-Balogh Péter P Keglevich György G

Beilstein journal of organic chemistry 20170112

A family of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides was synthesized by the microwave-assisted solvent-free addition of dialkyl phosphites and diphenylphosphine oxide, respectively, to imines formed from benzaldehyde derivatives and primary amines. After optimization, the reactivity was mapped, and the fine mechanism was evaluated by DFT calculations. Two α-aminophosphonates were subjected to an X-ray study revealing a racemic dimer formation made through a N-H···O=P intermo ...[more]

PMID: 28179951

Similar Datasets

Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles.

Project description:A microwave-assisted three-component protocol involving N-1 alkylation of 2-alkynylindoles with epichlorohydrin, ring opening of the epoxide with sodium azide, and an intramolecular Huisgen azide-internal alkyne 1,3-dipolar cycloaddition domino sequence has been described. The efficacy of the methodology has been demonstrated by treating various 2-alkynylindoles (aromatic/aliphatic) with epichlorohydrin and sodium azide furnishing annulated tetracyclic indolodiazepinotriazoles in satisfactory yields.

| S-EPMC3596043 | biostudies-other

Microwave-assisted synthesis of (aminomethylene)bisphosphine oxides and (aminomethylene)bisphosphonates by a three-component condensation.

Project description:A practical method was elaborated for the synthesis of (aminomethylene)bisphosphine oxides comprising the catalyst- and solvent-free microwave-assisted three-component condensation of primary amines, triethyl orthoformate and two equivalents of diphenylphosphine oxide. The method is also suitable for the preparation of (aminomethylene)bisphosphonates using (MeO)2P(O)H/(MeO)3CH or (EtO)2P(O)H/(EtO)3CH reactant pairs and even secondary amines. Several intermediates referring to the reaction mechanism together with a few by-products could also be identified.

| S-EPMC4979732 | biostudies-literature

Microwave-assisted synthesis of 3-nitroindoles from N-aryl enamines via intramolecular arene-alkene coupling.

Project description:A variety of N-aryl ?-nitroenamines were effectively transformed into 3-nitroindoles in good yields and with complete regioselectivity via a rapid microwave (?W) assisted intramolecular arene-alkene coupling reaction. This report further demonstrates the versatility of this method by constructing 3-carboalkoxy- and 3-cyanoindoles. Optimization data, substrate scope, and applications are discussed.

| S-EPMC3549302 | biostudies-literature

One-Pot Two-Step Synthesis of 2-Aryl benzimidazole <i>N</i>-oxides Using Microwave Heating as a Tool.

Project description:A methodology is reported for the preparation of 2-aryl-benzimidazole-3-oxide derivatives. By means of a one-pot two-step protocol, a library of 42 new compounds has been prepared. Reactions were performed in a total time of 40 min using microwave heating as a tool. A streamlined work-up process was also developed, allowing for facile isolation of the products. The methodology offers a more sustainable approach than previous routes, with only water and ethanol being used as solvents, and the products being isolated by means of a simple filtration without the need for any further purification.

| S-EPMC6832536 | biostudies-literature

Microwave-Assisted Knoevenagel-Doebner Reaction: An Efficient Method for Naturally Occurring Phenolic Acids Synthesis.

Project description:The common chemical method to synthesize Phenolic Acids (PAs) involves a relatively considerable energy intake. In order to solve this issue, microwave-assisted Knoevenagel-Doebner condensations were developed. Nevertheless, these synthetic procedures prove difficult to reproduce. Herein, we developed and optimized-by using a combination of a Design of Experiment and a standard optimization approach-a reliable procedure that converts naturally occuring p-hydroxybenzaldehydes into the corresponding PAs with conversions of 86-99% and in 85-97% yields.

| S-EPMC6156279 | biostudies-literature

Microwave-Assisted Synthesis of Nanoporous Aluminum-Based Coordination Polymers as Catalysts for Selective Sulfoxidation Reaction.

Project description:A series of aluminum-based coordination polymers or metal?organic frameworks (Al?MOFs), i.e., DUT-4, DUT-5, MIL-53, NH?-MIL-53, and MIL-100, have been facile prepared by microwave (MW)-assisted reactions and used as catalysts for selective sulfoxidation reactions. The MW-assisted synthesis drastically reduced the reaction time from few days to hours. The prepared MOFs have smaller and uniform particle sizes and better yield compared to conventional hydrothermal method. Furthermore, the Al?MOFs have been successfully demonstrated as catalysts in oxidation reaction of methyl phenyl sulfide with H?O? as oxidant, even under mild conditions, with more than 95% conversion.

| S-EPMC6418783 | biostudies-literature

Microwave-Assisted Synthesis of N-Phenylsuccinimide.

Project description:A microwave-assisted synthesis of N-phenylsuccinimide has been developed for the second-semester organic teaching laboratory. Utilizing this procedure, N-phenylsuccinimide can be synthesized by heating a mixture of aniline and succinic anhydride in a domestic microwave oven for four minutes in moderate yields (40-60%). This technique reduces the reaction time as compared to the traditional synthesis by several hours, which allows the preparation to be achieved in a single organic chemistry laboratory period. This reaction is performed in the absence of solvent, is energy efficient, and is atom economical; therefore, it represents a "greener" preparation than the traditional synthesis of N-phenylsuccinimide.

| S-EPMC3224042 | biostudies-literature

Microwave-assisted synthesis of rhodamine derivatives.

Project description:The microwave synthesis of 12 rhodamine-derived imines is described. The present work involves condensation of rhodamine hydrazide with various aromatic aldehydes in ethanol under microwave irradiation. The results obtained indicate that, unlike classical heating, microwave irradiation results in higher yields, shorter reaction time, mild reaction condition and simple work-up procedure. The structures of synthesized compounds were confirmed by 1H-NMR, 13C-NMR, FT-IR and high-resolution mass spectra data.

| S-EPMC7082095 | biostudies-literature

Microwave assisted synthesis of bridgehead alkenes.

Project description:A new, concise method to synthesize triene precursors for the type 2 intramolecular Diels-Alder reaction has been developed. Microwave irradiation of the trienes provides a convenient method for the synthesis of bridgehead alkenes. Higher yields, shorter reaction times, and lower reaction temperatures provide a general and efficient route to this interesting class of molecules.

| S-EPMC3064725 | biostudies-literature

Microwave-Assisted Synthesis of Mono- and Disubstituted 4-Hydroxyacetophenone Derivatives via Mannich Reaction: Synthesis, XRD and HS-Analysis.

Project description:An efficient microwave-assisted one-step synthetic route toward Mannich bases is developed from 4-hydroxyacetophenone and different secondary amines in quantitative yields, via a regioselective substitution reaction. The reaction takes a short time and is non-catalyzed and reproducible on a gram scale. The environmentally benign methodology provides a novel alternative, to the conventional methodologies, for the synthesis of mono- and disubstituted Mannich bases of 4-hydroxyacetophenone. All compounds were well-characterized by FT-IR, ¹H NMR, 13C NMR, and mass spectrometry. The structures of 1-{4-hydroxy-3-[(morpholin-4-yl)methyl]phenyl}ethan-1-one (2a) and 1-{4-hydroxy-3-[(pyrrolidin-1-yl)methyl]phenyl}ethan-1-one (3a) were determined by single crystal X-ray crystallography. Compound 2a and 3a crystallize in monoclinic, P2?/n, and orthorhombic, Pbca, respectively. The most characteristic features of the molecular structure of 2a is that the morpholine fragment adopts a chair conformation with strong intramolecular hydrogen bonding. Compound 3a exhibits intermolecular hydrogen bonding, too. Furthermore, the computed Hirshfeld surface analysis confirms H-bonds and ??? stack interactions obtained by XRD packing analyses.

| S-EPMC6384783 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data